An Awkward Encounter
by letmetemptyou19
Summary: Takes place while Crowley is working as Nanny Ashtoreth for the Dowlings. One night, Aziraphale makes a discovery that could change everything. (Crossdressing!Crowley). PWP


It had been an accident.

He really hadn't meant to cause any trouble.

Aziraphale rolled over and groaned into his pillow. He hadn't needed to glance over to know that the clock read 1:56 AM. It wasn't that Aziraphale _needed_ to sleep, he just rather liked it. The way Aziraphale felt about sleep was most comparable to how a human might feel about a hot bubble bath at the end of a long day; it was not at all necessary, but an exquisite opportunity to relax nonetheless. And Aziraphale quite needed an opportunity to relax after the incredibly awkward encounter that had happened just a few hours earlier.

At precisely 10:30pm that evening, Warlock Dowling drifted off into a quite pleasant state of unconsciousness thanks to his nanny's lullaby. Nanny Ashtoreth always had the strangest lullabies, but the unconventional lyrics did nothing to discount her soothing melodies. The nanny checked thrice that Warlock was really asleep. These days, the Destroyer of Worlds had made a nasty habit of skittering out of bed to play with his monster trucks the moment the door clicked shut behind her. It was hard enough getting him into bed at 8pm, never mind getting him to fall asleep in a reasonable amount of time. After ensuring the boy was not awake, she tiptoed out into the hallway, quietly pulled the door closed, and walked swiftly to her quarters just down the hall.

Crowley ripped the velvet calot off of his head as soon as he was in the door and shook out his red curls. He leaned back against the cool mahogany, looking up at the ceiling and letting out a deep sigh. He had known being the Antichrist's nanny would be difficult, but he'd assumed it would be because of the sheer evil gurgling deep within the child's twisted mind, not the fact that he was... well, a child. The job was only getting harder, too. The toddler years had been surprisingly easy, but now the child was four years old, with endless curiosity and an endless desire to disobey authority. Crowley was fascinated that one tiny person could fill up his day with so much chatter. All the demon could think about at this very moment was getting out of the stuffy, wool dress he had been chasing Warlock around in all afternoon. He removed his sunglasses, gloves, horrendous jacket, and shoes with haste before waving his hand and producing a perfectly folded dress on top of the wardrobe. Deciding it was folded a little too perfectly, Crowley grumbled and skewed the skirt ever so slightly. There. Now he was comfortable.

Crowley slinked over to the bed and sat down, still wearing the black silk slip with lace edging and sheer black stockings he had worn beneath his ensemble that day. Perhaps it was not entirely necessary for Crowley to commit so wholeheartedly to his role as Nanny Ashtoreth, but he found that wearing the undergarments helped him to stay in character, which he desperately needed to do if he wanted Warlock to have any chance at being a normal kid. Well, as normal as an Antichrist can be, anyway. And besides, it was much more comfortable than any men's underwear he'd worn to date. Crowley looked up at himself in the floor mirror that sat in the corner across from him and leaned back onto his elbows. He didn't like it. It was hard to look cold and menacing wearing lace, even for a demon. Still, he couldn't risk being woken up in the middle of the night by his ward while wearing a set of boxer briefs. His eyes flickered over to the dresser drawer that held a pair of black skinny jeans and a leather jacket. Sometimes he would put them on and saunter around his room just to feel like himself again. The whole world might come to an end in less than a decade, and here he was running around after a preschooler dressed like a half-baked Mary Poppins.

It had been a rough day, and though he did not age his body felt years older than it had this morning. He decided he'd take his chances and put on the leather jacket ensemble. The Dowlings had left this afternoon on official business in America, anyway. No risk of being caught by anyone who had the good sense to believe he was not the nanny he said he was. Just for a few minutes, he told himself. Then he'd go back to being the nanny for the next few weeks. He stood up and lifted his right leg onto the bed and slipped his fingers under the stocking's band.

He had no sooner began to roll it swiftly down his leg when Aziraphale burst into the room, breathing heavily.

"Crowley, I've finally done it! Warlock has finally - "

_"Angel!" _Crowley hissed as he grabbed the duvet cover off the bed to wrap quickly around his scantily clad body. Aziraphale became quite flustered.

"Oh! I'm so sorry, dear," said the angel, desperately trying to avert his gaze, but failing horribly as he could still see a bit of Crowley's slip peeking out from under the blanket. "I just wanted to tell you about... about what, er, happened earlier today – "

"Get OUT!"

"Yes! Yes, fine, I- I'm so sorry, Crowley, I really didn't intend... well goodnight," Aziraphale sputtered, breaking eye contact with the furious demon and hastily closing the door behind him. Crowley stood for a moment in shock about what had just happened. He should've locked the door when he got into the room, he thought. Why had he never thought to just lock the door? _No, _the demon thought to himself, _if Aziraphale wanted to barge into the room unannounced it was going to happen, lock or no lock. _He sunk down onto the bed, removed his other stocking, and wriggled up to his pillow, collapsing with the blanket still wrapped tightly around him. He had lost any desire to feel like himself again. Right now, he wanted to be literally anyone else in the world.

Aziraphale's thoughts whirred around in his head at a million miles a minute. What had just happened? He would've knocked first had he known Crowley was still awake, but he knew how much Crowley loved his sleep. He'd once slept through almost an entire century, and Aziraphale knew that if you had any hopes of waking him up, it involved moving about quite loudly and with the element of surprise. But Crowley hadn't been asleep, and Aziraphale had just pissed off one of the most powerful demons in hell. More importantly, he had embarrassed a dear friend. He slipped into his own bedroom and closed the door. _Think about literally anything else, Aziraphale, _the angel thought to himself as he flopped onto the bed. _The only way you could possibly make this worse is to dwell on it so long it gets seared into your brain. _It was no use, though. As hard as he tried, Aziraphale could not get the image of Crowley wearing that slip and stockings out of his head. With every blink, he remembered with laser-like intensity the soft, pale flesh of Crowley's inner thigh. Why did he have to wear something with a slit nearly up to the hip, anyway?

It wasn't that Aziraphale had never thought about Crowley in... _that way _before. He had always found the demon's preferred form rather attractive, and Crowley knew this. In fact, he reveled in it. It was half the reason he had insisted on wearing such tight pants for the last few decades, even after they'd fallen out of style in the 1990s. And it wasn't that Aziraphale hadn't seen Crowley nearly naked before, either. They'd been to the beach together, of course, but that had been a long time ago, when men and women still dressed rather modestly for a day on the water. This was different. He had never seen Crowley so vulnerable before, so _delicate. _It stirred a feeling in him that he had never felt so strongly before, a feeling that made him go tingly all over. The way Crowley had said "angel" burned in his ears for hours as the angel tried desperately and failed to fall asleep. As he began to drift off, the image of Crowley straddling his hips would drift into his mind and he would jerk awake, that same familiar feeling burning away in the pit of his stomach, right next to the overwhelming sense of guilt that lingered there as well. At 1:58AM, just as Aziraphale had decided that there was no use trying to sleep anymore, there was a knock at his door.

It appeared Crowley had not been able to sleep, either.

"Crowley! I - er, come in," Aziraphale said, opening the door wider.

Crowley slipped in through the door and walked past the angel to sit down at the foot of his bed. He was wearing a floor-length terrycloth robe now, and Aziraphale did not busy himself with any ideas of what he may be wearing underneath. Crowley sat for a minute staring at his hands in his lap, opening his mouth as if to say something before closing it again. He did this a couple of times before looking up to see Aziraphale's bright blue eyes gazing back at him from across the room.

"Aziraphale. I just wanted to tell you that... what you saw, Aziraphale, it wasn't... I'm sorry I yelled at you earlier," Crowley finally settled on sheepishly.

To be perfectly honest, Crowley wasn't entirely sure why he had come to Aziraphale's door. He just knew he wanted to talk to someone, and that someone was always his angel.

"You're sorry? Oh dear, don't be sorry, _I _am sorry," Aziraphale assured him. He crossed the small bedroom to sit down next to the demon. "I should've knocked. Really, I am so, so sorry that I barged in on a – well, an intimate moment," he said, glancing away.

"No, no," Crowley said, shifting his gaze back to the fidgeting hands in his lap.

Had he ever looked so nervous before? Aziraphale decided that he hadn't.

"I know you were just trying to wake me up. I may not be capable of dying, but I do know that I sleep like the dead," Crowley smirked.

"Heh," Aziraphale chuckled. "You are, of course, right about that."

"And anyways, it wasn't an intimate moment. I sleep like this every night. While I've been here, I mean."

So, there was Aziraphale's answer. _Like this, _the demon had said. He was almost certainly wearing the silky black chemise underneath his robe. Aziraphale felt a catch in his throat as he tried not to focus on this fact.

"Ah, well, jolly good. That's um... fine. Just fine. I mean, it's more than fine, not just fine. Not that I care what you sleep in, of course, I just – "

"Angel."

Crowley was staring at him now searchingly, his intense serpentine eyes glittering in the candlelight. Aziraphale did wish he would stop. It only made it harder for him to think. He could feel himself turning bright pink, remembering again the way Crowley had spoken to him earlier when he'd surprised him. Though he had never had one before, Aziraphale knew enough about humans to realize that he was experiencing the beginnings of his first-ever erection. So that's what that tingly feeling was. _Human bodies are lousy, they really are_, he thought. He wondered if Crowley would notice when to his horror, a look of revelation came across the demon's face. A small smirk crept onto Crowley's lips.

"Angel... would you like to see it again?"

"Erm..." Aziraphale crossed his legs, trying to look as prim as he could muster. "Well, I... I supposed I am rather curious about the type of fabric, actually."

"Fabric," Crowley chuckled, cocking a brow.

"Yes, well, one never knows what type of bowtie they might want to acquire next, you know," Aziraphale squeaked.

Crowley stood up and crossed the room so as to give Aziraphale the full effect. Without breaking eye contact he slowly untied the robe and shimmied it off of his shoulders onto the floor. Aziraphale, to his own dismay, let out a small gasp. It was the first time he'd gotten a proper look at Crowley wearing the slip, and he was overwhelmed. The way the lace grazed Crowley's thighs, the way the slit of the skirt conjoined at Crowley's hip, the way Crowley was _staring _at him right now... it all became a bit much.

"Crowley."

"Yes?"

"Come here."

Crowley sauntered towards him, his ridiculous walk only emphasized by the tight ensemble he wore now. Aziraphale reached out a hand and tentatively ran his thumb and forefinger across the lace hem. Crowley stood as still as possible, resisting the urge to lean into the angel's hand. He wanted to know how it felt to be touched by an angel, but he wanted Aziraphale to make that call for himself. Aziraphale let the hem glide through his fingers all the way to the slit, where he paused. He looked up to see Crowley gazing down at him, hardly breathing. _Fuck it, _the angel thought to himself as he slid his hand to the other side of the slit, grazing Crowley's thigh ever so gently. Crowley stifled a moan as his cock twitched. Aziraphale noticed. In an instant, he pulled the demon into his lap so that he was facing him, one arm wrapped tightly around his waist. He slid his hand up Crowley's thigh as the demon moaned into his ear. He was certainly breathing now. Crowley had to resist sinking his teeth into the soft skin beneath his mouth as he kissed lazily up and down Aziraphale's neck. Aziraphale's hand inched up further and the angel gasped as he realized that Crowley wasn't wearing anything at all underneath the slip. As his hand reached Crowley's hipbone, the demon couldn't stand it any longer. Crowley's lips crashed against Aziraphale's with enough force to send them both toppling backwards onto the bed.

Crowley could do weird things with his tongue. Weird, and quite exquisite, Aziraphale decided as Crowley's forked tongue explored the inside of his mouth. How was it that less than ten minutes ago he had been picturing this very moment, and now it was entirely tangible? His cock, now magnificently hard, strained against his trousers as Crowley writhed against his hips, lips still locked on his own. Without breaking their kiss, Crowley waved a hand and Aziraphale moaned deeply at the new sensation of flesh against flesh.

"_Fuck, _Crowley."

"Mmhmm," Crowley hummed into the angel's skin as he kissed his way down his chest, still twirling his hips against Aziraphale's hard length. Once he'd kissed as low as he could without changing his position, Crowley shifted himself in between Aziraphale's legs. Aziraphale knew what came next, and he became restless with anticipation. For the first time since he had disrobed, Crowley felt uncertain about how to proceed.

"Do you want me to-"

"Just put your cock in me already," Aziraphale growled, guiding Crowley into him. Crowley pushed into him as commanded, incredibly aroused by the way Aziraphale had taken charge. However, he didn't dare thrust his hips. He was nervous. The last thing he wanted was to hurt his angel.

"Crowley, come _on," _Aziraphale pleaded impatiently. Crowley didn't need any more encouragement than that. He began to rock his hips back and forth slowly. Aziraphale let out a moan so loud Crowley worried it might be heard by a Secret Serviceman down the hall, and attempted to muffle it with a kiss, which was only partly successful. Aziraphale was a virgin, although he was starting to wonder why he had never allowed himself to experience this. Waves of pleasure coursed through his body as Crowley pounded into him. He wrapped his hands around Crowley's ass and squeezed.

"Faster," Aziraphale breathed, and Crowley was all too happy to oblige. He quickened his thrusts, positively aching with desire. Aziraphale wrapped his legs around Crowley's waist, pulling him deeper. He knew he wouldn't last long. Crowley knew the same about himself. He slowed ever so slightly to shift his weight and grabbed Aziraphale's throbbing cock. He began to pump between them as he kissed the angel deeply.

There was a knock at the door. Aziraphale's eyes flew open as he simultaneously came into his own fist. There was no sign of Crowley, no robe on the floor, and Aziraphale realized that he must've fallen asleep after all. And what a wonderful dream had been having too. There was another knock, more urgent than the first.

"J- Just a minute," Aziraphale shouted as he scrambled out of the bed. He didn't know who it was, but he did know that he certainly couldn't have any evidence of what he'd just done lingering about. With a snap, the mess disappeared, and Aziraphale stood fully dressed in his clean, usual attire. He quickly crossed the room and took a deep breath before turning the knob and pulling the heavy mahogany door open.

"Angel. Hi. Can we talk?"


End file.
